Cubs get surprise Alex Bregman free agency boost from unexpected Red Sox voice

In the immediate aftermath of the Winter Meetings, it's felt like the Chicago Cubs are looking for a way to fit Alex Bregman into their 2026 plans and beyond. While that may mean capping their interest in Michael King, it also means making sure the Boston Red Sox pivot to a non-Bregman alternative.

The Red Sox have felt like the biggest threat to the Cubs for Bregman this offseason, but chatter out of Boston may change that. Red Sox content creator Jared Carrabis has teased that his hopes for a Bregman reunion in Boston might be dwindling.

While reminding his followers that situations during the offseason are always subject to change, referencing how there was an expectation Xander Bogaerts would return to the Red Sox before he inked his deal with the San Diego Padres, Carrabis admitted he doesn't feel good about Bregman's return.

Red Sox losing hope for Alex Bregman reunion could fuel Chicago Cubs' speculation.

As Cubs fans found last February, Bregman's free agency is all about reading context clues. For the Cubs, even on a pessimistic scale, they still have about $30 million to add this offseason before Opening Day. Optimistically, the number could be closer to $40 million. In other words, the Cubs' falling back in the sweepstakes for King could just mean they want to make sure they have the available dollars for a Bregman contract.

Similarly, it seems that the Red Sox have focused on looking at alternative options to address their need for offense. Boston has been heavily rumored to be involved in the trade talks for Arizona Diamondbacks' All-Star Ketel Marte, and they have also been linked to a potential trade for Willson Contreras.

There's also the belief that, like the Cubs, the Red Sox have some aversion to long-term deals. While Craig Breslow likely learned that from Jed Hoyer, it's worth pointing out that the Cubs did offer Bregman a four-year deal last offseason. That likely is the floor for their offer this time around, but given how open their books are after 2026, it wouldn't be crazy to think the Cubs would be willing to go to a fifth year.

We've been down this road last February--there was a time when it looked like the Cubs were going to push a Bregman deal across the finish line. That feeling has returned, hopefully without the disappointment this time.